Are neighbors friendly in Drayden, MD?

As of early 2026, 100% of users say neighbors are friendly

Are there community events in Drayden, MD?

As of early 2026, 100% of users say there are community events

Are yards well-kept in Drayden, MD?

As of early 2026, 100% of users say yards are well-kept

Is there wildlife in Drayden, MD?

As of early 2026, 100% of users say there's wildlife

Is a car needed in Drayden, MD?

As of early 2026, 100% of users say car is needed

Would people walk alone at night in Drayden, MD?

As of early 2026, 100% of users say people would walk alone at night

Is Drayden, MD dog-friendly?

As of early 2026, 100% of users say it's dog friendly

Do kids play outside in Drayden, MD?

As of early 2026, 50% of users say kids play outside

Is Drayden, MD walkable to restaurants?

As of early 2026, 33% of users say it's walkable to restaurants

What is 18445 Windmill Point Rd estimated to be worth?

Trulia's estimated value for 18445 Windmill Point Rd in Drayden, MD is $389,200 .

What is the price history for 18445 Windmill Point Rd?

18445 Windmill Point Rd in Drayden, MD last sold for $230,000 in November 2016.

Is Drayden a buyer's or seller's market?

Drayden is currently a seller's market, based on recent for-sale activity.

What are the closest schools to 18445 Windmill Point Rd?

The closest schools to 18445 Windmill Point Rd in Drayden, MD are Leonardtown High School (rated 5/10), Piney Point Elementary School (Pre-K, rated 9/10), Spring Ridge Middle School (rated 5/10).

How big is the lot at 18445 Windmill Point Rd?

The lot at 18445 Windmill Point Rd in Drayden, MD is about 3 acres .

Does 18445 Windmill Point Rd have a garage?

Yes, 18445 Windmill Point Rd in Drayden, MD has a garage.

OFF MARKET

18445 Windmill Point Rd
Drayden, MD 20630

3 Beds
2 Baths
1,584 sqft (on 3 acres)

$389,200

Trulia Estimate

as of Aug 9, 2026

Est. Refi. Payment $2,314/mo*

Refinance Your Home

$389,200

Trulia Estimate

as of Aug 9, 2026

Est. Refi. Payment $2,314/mo*

Refinance Your Home

3 Beds

2 Baths

1,584 sqft

(on 3 acres)

Local Information

Map ViewExplore the area around 18445 Windmill Point Rd.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Property Type

Single-Family Home

Year Built

1944

Lot Size

3 acres

Living Area

1,584 sqft

Price/Sqft

$246

Parking

Garage

About this House

A rare find, An affordable move-in ready home on mostly cleared 3 acre lot, with beautiful shade trees at the end of the road for privacy. 32X28 garage is a mechanics dream, Field on the side offers many uses, Entertain on large deck Woodstove with a brick surround for those winter nights. Updated kitchen with corian counters & tile floors. Recently replaced roof shingles and HVAC . Take a look!

18445 Windmill Point Rd, Drayden, MD 20630 is a 3 bedroom, 2 bathroom, 1,584 sqft single-family home built in 1944. It last sold for $230,000 on Nov 10, 2016. It is currently off market. The Trulia Estimate is $389,200, with a rent estimate of $2,312/month.

Home Details for 18445 Windmill Point Rd

Interior Features
Heating & Cooling Heating: Heat PumpAir ConditioningHeating Fuel: Heat Pump
Levels, Entrance, & Accessibility Stories: 1
Appliances & Utilities DishwasherMicrowaveRefrigerator
Fireplace & Spa Fireplace

Exterior Features
Exterior Home Features Roof: Shake ShingleDeckExterior: Vinyl
Parking & Garage GarageParking: Garage Attached

Property Information
Year Built Year Built: 1944
Property Type / Style Property Type: Single Family HomeArchitecture: Conventional

Community
Units in Building: 1

Lot Information
Lot Area: 3.00 acres

Price History for 18445 Windmill Point Rd

Date	Price	Event	Source
11/10/2016	$230,000	Sold	N/A
Recording Date 11/10/2016 Contract Date 10/31/2016 County Transfer Tax $2,000 Total Transfer Tax $2,575
08/22/2016	$235,000	Listed For Sale	Agent Provided

06/28/2012	$196,000	Sold	N/A
Recording Date 06/28/2012 Contract Date 05/01/2012 County Transfer Tax $600 Total Transfer Tax $1,090
03/30/2012	$199,900	PriceChange	Agent Provided
Price Change $90 (-0%)
03/29/2012	$199,990	Pending	Agent Provided

03/20/2012	$199,990	PriceChange	Agent Provided
Price Change $199,990 (0%)
03/18/2012	$0	Listed For Sale	Agent Provided

02/01/2012	$149,900	ListingRemoved	Agent Provided

11/24/2011	$149,900	PriceChange	Agent Provided
Price Change $10,000 (-6%)
11/12/2011	$159,900	PriceChange	Agent Provided
Price Change $15,000 (-9%)
10/26/2011	$174,900	PriceChange	Agent Provided
Price Change $25,000 (-13%)
09/21/2011	$199,900	PriceChange	Agent Provided
Price Change $199,900 (0%)
09/14/2011	$0	Listed For Sale	Agent Provided

06/29/2011	$289,197	Sold	N/A
Recording Date 06/29/2011 County Transfer Tax N/A Total Transfer Tax N/A
05/23/2005	$232,000	Sold	N/A
Recording Date 05/23/2005 County Transfer Tax N/A Total Transfer Tax N/A
01/07/1997	$110,000	Sold	N/A
Recording Date 01/07/1997 County Transfer Tax N/A Total Transfer Tax N/A

Market trends in Drayden

Last updated June 2026

Avg. sale price

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Sale-to-List Price

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Price per sq ft

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Available listings

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Property Tax and Assessment

Year	2025
Tax	$2,909
Assessment	$260,200

Home facts updated by county records

Comparable Sales for 18445 Windmill Point Rd

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
46442 Hyatt Ct, Drayden, MD	0.65	Single-Family Home	$635,000	02/26/26	4	3.5	3,534
18747 Vernon Ct, Drayden, MD	0.58	Single-Family Home	$640,000	05/11/26	4	2.5	3,572
46210 Lisa Marie Ct, Drayden, MD	1.05	Single-Family Home	$660,000	06/15/26	4	3	2,486
46219 Stasha Ct, Drayden, MD	1.22	Single-Family Home	$772,338	09/05/25	3	2.5	2,350
45903 Burns Dr, Valley Lee, MD	1.82	Single-Family Home	$450,000	05/27/26	3	2	1,964
19211 Nelson Ct, Valley Lee, MD	1.60	Single-Family Home	$555,000	06/12/26	4	2.5	2,184
19005 N Porto Bello Dr, Drayden, MD	1.07	Single-Family Home	$660,000	07/24/26	5	3.5	4,022
45810 Aberdeen Ln, Valley Lee, MD	1.94	Single-Family Home	$397,000	12/19/25	3	2	1,350
46219 Shasha Ct, Drayden, MD	1.22	Single-Family Home	$772,338	08/22/25	4	3.5	2,350
19201 Nelson Ct, Valley Lee, MD	1.55	Single-Family Home	$591,500	09/04/25	4	3.5	2,953

Nearby homes

Get a sense of prices in the area by checking nearby homes.

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OFF MARKET
Est. $232,800
3 bd
2 ba
1,152 sqft
18459 Windmill Point Rd,
Drayden, MD 20630
Coldwell Banker Jay Lilly Real Estate
OFF MARKET
Dockside Ln,
Drayden, MD 20630
OFF MARKET
Est. $710,500
4 bd
2.5 ba
3,448 sqft
46441 Porto Bello Ct,
Drayden, MD 20630
O'Brien Realty ERA Powered
OFF MARKET
Est. $720,300
5 bd
3 ba
3,462 sqft
46461 Porto Bello Ct,
Drayden, MD 20630
CENTURY 21 New Millennium
SOLD
MAY 11, 2026
$640,000
4 bd
2.5 ba
3,572 sqft
18747 Vernon Ct,
Drayden, MD 20630
RE/MAX Realty Group
SOLD
MAR 25, 2026
$250,000
18465 Cherryfield Rd,
Drayden, MD 20630
JPAR Real Estate Professionals
OFF MARKET
18361 Cherryfield Rd,
Drayden, MD 20630
Irvin Realty LLC
SOLD
FEB 26, 2026
$635,000
4 bd
3.5 ba
3,534 sqft
46442 Hyatt Ct,
Drayden, MD 20630
RE/MAX Realty Group
OFF MARKET
Est. $814,400
4 bd
4.5 ba
5,298 sqft
18760 Vernon Ct,
Drayden, MD 20630
CENTURY 21 New Millennium
OFF MARKET
Est. $392,900
3 bd
2 ba
1,864 sqft
18631 Cherryfield Rd,
Drayden, MD 20630
CENTURY 21 New Millennium
OFF MARKET
3 Mount Pleasant Farms,
Drayden, MD 20630
EXP Realty, LLC
SOLD
MAR 13, 2026
$152,000
4 Mount Pleasant Farms,
Drayden, MD 20630
EXP Realty, LLC

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Additional Cost

Assigned Schools

These are the assigned schools for 18445 Windmill Point Rd.

View nearby schools on GreatSchools

The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Drayden

At least 1 Trulia users voted on each feature.

100 % Say neighbors are friendly
100 % Say there are community events
100 % Say yards are well-kept
100 % Say there's wildlife
100 % Say car is needed
100 % Say people would walk alone at night
100 % Say it's dog friendly
50 % Say kids play outside
33 % Say it's walkable to restaurants

Sourced by Trulia users. Learn more about our methodology.

LGBTQ Local Legal Protections

Apartments for Rent

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$1,390/mo
1 bd
1 ba
Potomac Pines | 17476 Piney Point Rd,
Piney Pt, MD 20674
$1,795/mo
2 bd
1 ba
Address Not Disclosed,
Tall Timbers, MD 20690
$1,495/mo
1 bd
1 ba
Address Not Disclosed,
Tall Timbers, MD 20690
PET FRIENDLY
$1,390/mo
1 bd
1 ba
17476 Piney Point Rd #6,
Piney Pt, MD 20674
See more homes for rent in
Drayden
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Homes for sale near 18445 Windmill Point Rd

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NEW CONSTRUCTION
1.09 ACRES
$635,900
3 bd
2.5 ba
2,240 sqft
19103 Windsor Ct,
Drayden, MD 20630
RE/MAX One
NEW CONSTRUCTION
1.03 ACRES
$679,900
4 bd
2.5 ba
2,643 sqft
46234 Stasha Ct,
Drayden, MD 20630
RE/MAX One
NEW CONSTRUCTION
1.26 ACRES
$776,220
3 bd
3.5 ba
2,253 sqft
19166 N Porto Bello Dr,
Drayden, MD 20630
RE/MAX One
NEW CONSTRUCTION
1.24 ACRES
$599,900
4 bd
2.5 ba
2,343 sqft
19163 Porto Bello,
Drayden, MD 20630
RE/MAX One
1.14 ACRES
$585,000
4 bd
3.5 ba
3,436 sqft
19335 Greens Crossing Ct,
Great Mills, MD 20634
CENTURY 21 New Millennium
1 ACRE
$529,000
3 bd
2 ba
1,371 sqft
47558 Lucas Cove Ln,
Lexington Park, MD 20653
Infinitas Realty Group
189 ACRES
$3,500,000
3 bd
2 ba
4,541 sqft
45776 Boothe Rd,
Drayden, MD 20630
Century 21 Redwood Realty
1.72 ACRES
$1,900,000
4 bd
3.5 ba
5,747 sqft
19393 N Snow Hill Manor Rd,
Lexington Park, MD 20653
Long & Foster Real Estate, Inc.
NEW - 1 DAY AGO
3.42 ACRES
$460,000
4 bd
2 ba
2,001 sqft
17773 Piney Point Rd,
Tall Timbers, MD 20690
CENTURY 21 New Millennium
COMING SOON 9/1
42 ACRES
$2,250,000
4 bd
3 ba
4,228 sqft
45433 Drayden Rd,
Valley Lee, MD 20692
Century 21 Redwood Realty
See more homes for sale in
Drayden
Take a look

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Off Market Homes Near 18445 Windmill Point Rd

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SOLD
JUL 30, 2026
$419,000
4 bd
3 ba
2,160 sqft
20166 Manor Dr,
Park Hall, MD 20667
The Southside Group Real Estate
SOLD
JUL 29, 2026
$305,000
2 bd
1 ba
1,030 sqft
44328 Tall Timbers Rd,
Tall Timbers, MD 20690
RE/MAX One
SOLD
JUL 22, 2026
$220,000
3 bd
2 ba
1,300 sqft
20827 Primrose Ct,
Lexington Park, MD 20653
Real Broker, LLC
SOLD
JUL 21, 2026
$410,000
3 bd
2 ba
3,246 sqft
48050 Freehold Dr,
Lexington Park, MD 20653
SOLD
JUL 20, 2026
$326,000
5 bd
2.5 ba
2,612 sqft
18091 Point Lookout Rd,
Park Hall, MD 20667
Infinitas Realty Group
SOLD
JUL 17, 2026
$280,000
2 bd
2 ba
1,260 sqft
23510 Franklin D Roosevelt Blvd #304,
Drayden, MD 20630
SOLD
JUL 14, 2026
$375,000
4 bd
4 ba
2,950 sqft
47843 Yaocomico Ln,
Lexington Park, MD 20653
CENTURY 21 New Millennium
SOLD
JUL 10, 2026
$280,000
2 bd
1 ba
800 sqft
17279 Piney Point Rd,
Piney Point, MD 20674
CENTURY 21 New Millennium
SOLD
JUL 9, 2026
$350,000
3 bd
1 ba
1,604 sqft
18792 McKays Beach Rd,
Leonardtown, MD 20650
SOLD
JUL 8, 2026
$230,000
3 bd
2 ba
1,300 sqft
20803 Primrose Ct,
Lexington Park, MD 20653
CENTURY 21 New Millennium
See more homes for sale in
Drayden
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Frequently asked questions about 18445 Windmill Point Rd

What is 18445 Windmill Point Rd estimated to be worth?
Trulia's estimated value for 18445 Windmill Point Rd in Drayden, MD is $389,200.
What is the price history for 18445 Windmill Point Rd?
18445 Windmill Point Rd in Drayden, MD last sold for $230,000 in November 2016.
Is Drayden a buyer's or seller's market?
Drayden is currently a seller's market, based on recent for-sale activity.
What are the closest schools to 18445 Windmill Point Rd?
The closest schools to 18445 Windmill Point Rd in Drayden, MD are Leonardtown High School (rated 5/10), Piney Point Elementary School (Pre-K, rated 9/10), Spring Ridge Middle School (rated 5/10).
How big is the lot at 18445 Windmill Point Rd?
The lot at 18445 Windmill Point Rd in Drayden, MD is about 3 acres.
Does 18445 Windmill Point Rd have a garage?
Yes, 18445 Windmill Point Rd in Drayden, MD has a garage.

18445 Windmill Point Rd
Drayden, MD 20630

$389,200

$389,200